tert-butyl 5-cyano-2-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxymethyl]indole-1-carboxylate | 1017279-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 5-cyano-2-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxymethyl]indole-1-carboxylate
• CAS: 1017279-73-0
• 化学式: C₂₆H₂₈N₂O₇
• 分子量: 480.518
• InChiKey: UQWHMZAKERPBMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  112.92
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-cyano-2-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxymethyl]indole-1-carboxylate 以63%的产率得到3-(3-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-yl)-2-methyl-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Modular Synthesis of Candidate Indole-based Insulin Mimics by Claisen Rearrangement

  摘要：

  A modular synthetic route to (indolyl)kojic acid anti-diabetes agents has been developed. Sonogashira coupling of a protected iodoaniline with a propargyl kojate was used to construct an (indole)methyl kojate. Its heteroaromatic Claisen rearrangement, followed by tautomerization to return the indole and pyrone rings, was used to create the biaryl C-C bond. This route should enable collections of insulin mimic drug candidates to be prepared from a few basic building blocks.

  DOI：

  10.1021/ol800058d
• 作为产物：
  描述：

  tert-butyl (4-cyano-2-iodo-phenyl)carbamate 、 5-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 四丁基氟化铵 作用下， 以 苯 、 四氢呋喃 为溶剂， 反应 13.0h， 以70%的产率得到tert-butyl 5-cyano-2-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxymethyl]indole-1-carboxylate
  参考文献：
  名称：

  Modular Synthesis of Candidate Indole-based Insulin Mimics by Claisen Rearrangement

  摘要：

  A modular synthetic route to (indolyl)kojic acid anti-diabetes agents has been developed. Sonogashira coupling of a protected iodoaniline with a propargyl kojate was used to construct an (indole)methyl kojate. Its heteroaromatic Claisen rearrangement, followed by tautomerization to return the indole and pyrone rings, was used to create the biaryl C-C bond. This route should enable collections of insulin mimic drug candidates to be prepared from a few basic building blocks.

  DOI：

  10.1021/ol800058d